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化学进展 DOI: 10.7536/PC121244 前一篇   后一篇

• 综述与评论 •

功能离子液体在Michael加成中的应用

刘硕1, 应安国*2, 倪宇翔1, 杨建国2, 许松林*1   

  1. 1. 天津大学化工学院 天津 300072;
    2. 台州学院医药化工学院 台州 318000
  • 收稿日期:2012-12-01 修回日期:2013-03-01 出版日期:2013-08-25 发布日期:2013-06-13
  • 通讯作者: 应安国,许松林 E-mail:agying@tzc.edu.cn;slxu@tju.edu.cn
  • 基金资助:

    国家自然科学基金项目(No.21106090)和中国博士后基金面上项目(No.2012M511352)资助

Application of Task-Specific Ionic Liquids to Michael Additions

Liu Shuo1, Ying Anguo*2, Ni Yuxiang1, Yang Jianguo2, Xu Songlin*1   

  1. 1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072;
    2. School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
  • Received:2012-12-01 Revised:2013-03-01 Online:2013-08-25 Published:2013-06-13

离子液体具备不可燃性、低挥发性、良好的溶解性能、可设计性和可重复使用性等特点,因此作为催化剂、促进剂或反应介质被广泛应用于有机合成领域中。本文从不同类型的离子液体角度,分别介绍了近年来酸性、碱性和手性功能离子液体在Michael加成反应中的应用研究,并对功能离子液体的结构特点、催化活性以及可能的催化反应机理方面展开了详细的评述。

Ionic liquids (ILs) have been widely applied as catalysts, promoters and/or reaction medium in organic synthesis due to their non-flammability, low volatility, good solubility, readily tunable catalytic activities and good recyclability. Herein, the recent advances on the applications of acidic task-specific ionic liquids (TSILs), basic TSILs and chiral TSILs in Michael addition have been reviewed. Moreover, the structure, catalytic activity and probable reaction mechanism of ILs are also fully discussed. Contents
1 Introdnction
2 Acidic ionic liquids
3 Basic ionic liquids
4 Chiral ionic liquids
5 Conclusion

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[1] Miao W, Chan T H. Acc. Chem. Res., 2006, 39: 897-908
[2] Wassercheid P, Keim W. Angew Chem. Int. Ed., 2000, 39: 3772-3789
[3] (a)Zhang Q, Zhang S, Deng Y. Green Chem., 2011, 13: 2619-2637;(b) 应安国(Ying A G), 叶伟东(Ye W D), 刘泺(Liu L), 吴国锋(Wu G F), 陈新志(Chen X Z), 钱胜(Qian S), 张秋萍(Zhang Q P). 有机化学(Chin. J. Org. Chem.), 2008, 28: 2081-2094
[4] (a)Jiang T F, Gu Y L, Liang B, Li J B, Shi Y P, Ou Q Y. Anal. Chim. Acta, 2003, 479: 249-254; (b)Wang J H, Cheng D H, Chen X W, Du Z, Fang Z L. Anal. Chem., 2007, 79: 620-625; (c)张晓果(Zhang X G), 周庆祥(Zhou Q X). 河南师范大学学报(自然科学版)(Journal of Henan Normal University, Natural Science Edition), 2010, 38: 109-112
[5] (a)Zane D, Raffaele A, Curulli A, Appetecchi G B, Passerini S. Electrochem. Commun., 2007, 9: 2037-2040; (b)Yoshizawa M, Narita A, Ohno H. Aust. J. Chem., 2004, 57: 139-144
[6] (a)Susan M A, Kaneko T, Noda A, Watanabe M. J. Am. Chem. Soc., 2005, 127: 4976-4983; (b)Lin I J B, Vasam C S. J. Organomet. Chem., 2005, 690: 3498-3512
[7] James H, Davis J. Chem. Lett., 2004, 33: 1072-1077
[8] Guo H C, Ma J A. Angew. Chem. Int. Ed., 2006, 45: 354-366
[9] Berner O M, Tedeschi L, Enders D. Eur. J. Org. Chem., 2002, 1877-1894
[10] Banik B K, Becker F F, Banik I. Bioorg. Med. Chem., 2004, 12: 2523-2528
[11] Budriesi R, Carosati E, Chiarini A, Cosimelli B, Cruciani G, Ioan P, Spinelli D, Spisani R. J. Med. Chem., 2005, 48: 2445-2456
[12] Calter M A, Liao W. J. Am. Chem. Soc., 2002, 124: 13127-13129
[13] 魏晓飞(Wei X F), 杜创(Du C), 王任(Wang R), 苗卿华(Miao Q H), 王萍(Wang P), 李春元(Li C Y), 王智(Wang Z), 王磊(Wang L). 分子催化(J. Mol. Cat.), 2009, 23: 273-276
[14] Nazira K, Liu X H, Petra L, Dimitrios P, Grace S. Tetrahedron, 2006, 62: 11039-11043
[15] Yu C J, Liu C J. Molecules, 2009, 14: 3222-3228
[16] Liu C J, Yu C J. Molecules, 2010, 15: 9197-9204
[17] Guo H, Li X, Wang J L, Jin X H, Lin X F. Tetrahedron, 2010, 66: 8300-8303
[18] Zhang Q Y, Xu J M, Chen W Q, Wu Q, Lin X F. Synlett, 2008, 5: 679-682
[19] 郭辉(Guo H), 王君良(Wang J L), 李霞(Li X), 吕德水(Lv D S), 林贤福(Lin X F). 催化学报(Chinese Journal of Catalysis), 2011, 32: 162-165
[20] Liu X, Lu M, Gu G, Lu T. J. Iran. Chem. Soc., 2011, 8: 775-781
[21] Minoo D, Peyman S, Mahboobeh B, Mostafa B. Monatsh Chem., 2012, 143: 109-112
[22] Bedos P, Amblard M, Subra G, Dodey P, Luccarini J M, Paquet J L, Pruneau D, Aumelas A, Martinez J. J. Med. Chem., 2000, 43: 2387-2394
[23] Han F, Yang L, Li Z, Xia C G. Org. Biomol. Chem., 2012, 10: 346-354
[24] Rajanarendar E, Govrardhan R K, Sivarami R A, Nagi R M. Green Chemistry Letters and Reviews, 2012, 5: 699-705
[25] 唐应彪(Tang Y B), 李雪辉(Li X H). 广东化工(Guangdong Chemical Industry), 2006, 33: 33-36
[26] Ranu B C, Banerjee S. Org. Lett., 2005, 7: 3049-3052
[27] Ranu B C, Banerjee S, Jana R. Tetrahedron, 2007, 63: 776-782
[28] Yang L, Xu L W, Zhou W, Li L, Xia C G. Tetrahedron Lett., 2006, 47: 7723-7726
[29] Xu J M, Qian C, Liu B K, Wu Q, Lin X F. Tetrahedron, 2007, 63: 986-990
[30] Xu J M, Wu Q, Zhang Q Y, Zhang F, Lin X F. Eur. J. Org. Chem., 2007, 1798-1802
[31] Massimo F, Vittorio L, Marco N, Alvise P, Maurizio S. Chem. Eur. J., 2009, 15: 12273-12282
[32] Liang D P, Xin X, Gao H, Duan H F, Lin Y J. Chem. Res. Chin. Univ., 2009, 25(2): 169-172
[33] Xin X, Wang Y, Xu W, Lin Y J, Duan H F, Dong D W. Green Chem., 2010, 12: 893-898
[34] Ying A G, Liu L, Wu G F, Chen G, Chen X Z, Ye W D. Tetrahedron Lett., 2009, 50: 1653-1657
[35] Ying A G, Wang L M, Deng H X, Chen J H, Chen X Z, Ye W D. ARKIVOC, 2009, (xi): 288-298
[36] 应安国(Ying A G), 郑人华(Zheng R H), 武承林(Wu C L), 梁华定(Liang H D), 葛昌华(Ge C H), 蒋华江(Jiang H J). 有机化学(Chinese Journal of Organic Chemistry), 2011, 31: 1312-1318
[37] Chen X W, Li X H, Song H B, Qian Y, Wang F R. Tetrahedron Lett., 2011, 52: 3588-3591
[38] Salvi P P, Mandhare A M, Sartape A S, Pawar D K, Han S H, Kolekar S S. C. R. Chimie, 2011, 14: 878-88
[39] Shaterian H R, Arman M, Rigi F. Journal of Molecular Liquids, 2011, 158: 145-150
[40] Wu L Y, Yan Z Y, Xie Y X, Niu Y Z, Liang Y M. Tetrahedron: Asymmetry, 2007, 18: 2086-2090
[41] Yang S D, Shi Y, Sun Z H, Zhao Y B, Liang Y M. Tetrahedron: Asymmetry, 2006, 17: 1895-1900
[42] Yang S D, Wu L Y, Yan Z Y, Pan Z L, Liang Y M. J. Mol. Catal. A: Chem., 2007, 268: 107-111
[43] Li P H, Wang L, Wang M, Zhang Y C. Eur. J. Org. Chem., 2008, 1157-1160
[44] Li P H, Wang L, Zhang Y C, Wang G W. Tetrahedron, 2008, 64: 7633-7638
[45] Qian Y B, Xiao S Y, Liu L, Wang Y M. Tetrahedron: Asymmetry, 2008, 19: 1515-1518
[46] Ni B K, Zhang Q Y, Headley A D. Green Chem., 2007, 9: 737-739
[47] Wang J, Li H, Lou B, Zu L, Guo H, Wang W. Chem. Eur. J., 2006, 12: 4321-4332
[48] Zhang Q Y, Ni B K, Headley A D. Tetrahedron, 2008, 64: 5091-5097
[49] Ni B K, Zhang Z Q, Kritanjali D, Headley A D. Org. Lett., 2009, 11(4): 1037-1040
[50] Ni B K, Zhang Z Q, Headley A D. Tetrahedron Lett., 2008, 49: 1249-1252
[51] Truong T K, Vo-Thanh G. Tetrahedron, 2010, 66: 5277-5282
[52] Wang W H, Wang X B, Kodama K, Hirose T, Zhang G Y. Tetrahedron, 2010, 66: 4970-4076
[53] Maltsev O V, Kucherenko A S, Beletskaya I P, Tartakovsky V A, Zlotin S G. Eur. J. Org. Chem., 2010, 2927-2933
[54] Xu D Z, Liu Y J, Shi S, Wang Y M. Tetrahedron: Asymmetry, 2010, 21: 2530-2534
[55] Wang G, Sun H C, Cao X H. Catal. Lett., 2011, 141: 1324-1331
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